The purpose of this essay is to explore the relationship between the simple and the complex in economics by anchoring our analysis on bounded rationality. Much of the conventional literature focuses on ‘un-bounded rationality’ of the rationality-as-consistency variety. Theorizing of bounded rationality tends to assume that the problem to be solved is independent of the nature of bounded rationality. Following the insights from the works of Herbert Simon and contributions from outside economics, both bounded rationality and the environment are inextricably linked. The boundaries between bounded rationality and its environment can shift. The form in which bounded rationality is found depends on the complexity of the environment. Furthermore, if local interactions between bounded rational agents result in the formation of hierarchies – the complexity of the collective system will change. Whether this will occur depends on the nature of bounded rationality at the individual level.